


Snap-shots From the Life of Dean Winchester

by notspicy



Category: Supernatural
Genre: Abusive John Winchester, Episode Fix-It: s15e20 Carry On, F/M, Growing Up, High School, Implied/Referenced Self-Harm, Implied/Referenced Sex, Implied/Referenced Suicide, Kid Fic, M/M, Quote: Saving people hunting things (Supernatural), Sexuality Crisis, implied sex work, john winchester hate club plz stand up, mostly just snippets of the boys growing up and kinning dean lol, pretty lowkey destiel, the general bloodyness of supernatural, the winchester boys growing up
Language: English
Status: Completed
Published: 2020-12-03
Updated: 2020-12-03
Packaged: 2021-03-09 18:47:08
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 4
Words: 7,673
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/27851094
Author URL: https://archiveofourown.org/users/notspicy/pseuds/notspicy
Summary: “He’s your big brother Sammy.” Bobby smiles. Sam looks up carefully. “Whether you like it or not, if he’s anything like I know him to be: you’re gonna be owing your brother big time for the rest of your lives.”Sam chuckles. “Yeah. I can take care of myself, though.”Bobby sighs. “Sure you can, boy.”Dean tries not to smile, and give himself away.--A few moments in the life (and death) of Dean Winchester.
Relationships: Blurry Woman (Supernatural: Carry On)/Sam Winchester, Cassie Robinson/Dean Winchester, Castiel/Dean Winchester
Comments: 4
Kudos: 58





	1. Just a Kid

**Author's Note:**

> From age 4 to high school.

“Just watch your brother.” Dad says. Dean is already holding Sammy. They don’t have a cradle in this hotel, Dad says. Says some other family is using it.

Dean just nods, without looking.

Dad grabs his face. Hard.

“You don’t open that door. You don’t talk to anybody. You stay right here until I come back.”

Dad lets go of Dean’s face, leaving fingerprints on his baby face.

“Mhm Daddy.” He mumbles.

And then Dad leaves, and Dean is alone for a long time.

He can’t read clocks yet. Is still figuring out numbers past 11. He doesn’t understand why Sammy can’t eat anything yummy.

So Dean, barely five, stays up all night; holding baby Sammy very very tight, curled up between two scratchy pillows and the headboard, with the sound on the TV so low he can’t even hear it. He can’t read, but the people on the TV don’t seem unhappy. They seem very happy.

He wishes Daddy could be happy again.

* * *

Kindergarten does not go well for Dean. Neither does 1st, or 2nd, or third grade. He’s gone to six schools. Twice because people came to where they were staying and freaked Dad out. Three times because Dean said something bad. Once because they picked up, moved, and Dad told him not to tell anyone anything, and that he had to bring him and Sammy home every day.

Everyone else in his third grade class is much better at reading than him. And math. And everything else. Dean gets recess detention a lot at this new school, but it's not that bad because his teacher is pretty cool. 

“Mr. Winchester- I promise it will only be a few minutes-“ Ms. Samantha puts her hand on Dad's arm. “Just a few minutes.”

Dad came to their school, getting them out of class. Dean is sure there's something wrong. 

Dad rolls his eyes, big, and points to the chair at the front of the office. “Sit.”

He takes Sammy’s hand and they  _ sit _ .

“I wish you had come to conferences.” Ms. Samantha whispers, from around the corner. Dean doesn’t  _ want _ to eves-drop, but he can’t help himself. “Dean is really a smart kid. He really is. He’s just... behind, and I can’t even blame him.”

Dean grips the chair tightly.

Dad doesn’t say anything yet.

“He’s been too six? Six schools?... his foundational education has been completely disrupted and,” 

Dad coughs. And Sammy looks up at Dean. 

“Obviously, I am sure you’ve done your best, but I really think he would benefit greatly from even a- a year, a few months, of stable education. I’ll tutor him.” Ms. Samantha pleads. She looks small in comparison to Dad. Intimidating. 

Dean realizes nobody, not even Dad, is ever gonna look out for him other than him. 

Dad pushes his shoulders back, stuffing a hand in his pocket. “Lady, I’ve got a handle on my own damn kids. We have to go.” 

“Is there anyone else they could stay with? Mom? Or a grandparent?” 

Dad looks offended, before turning his back on her. 

He grabs Dean by the back of the collar, and he never sees Ms. Samantha again. 

* * *

“Dean! Dean!” Sam yells, thrashing around in bed. He shoots up, eyes wild and wide, crying. Dean turns over in bed, and puts a hand around Sam. 

“Shh, shh.” Dean rubs Sam’s back, feeling his breathing slow. “It’s okay Sammy.” 

Dad is out tonight. There's a low glow of a motel TV lighting up both their faces. 

“You have a bad dream?” Dean whispers, as Sam leans into his shoulder. He nods. 

“Mhm.” Sam rubs his eyes, his little hands shaking. “Clowns.” 

Dean gives a sympathetic groan, rubbing the sleep from his eyes. 

Dean is exhausted. School is long, taking care of Sam is longer. He hadn’t been asleep longer than two hours when Sam woke him up. But- he rubs Sam’s back, lets his breathing even out, and feels him fall asleep on his shoulder. 

Sam just started 3rd grade. Dean in 5th. 

Most boys grow out of nightmares by then. 

Dean can’t fall back asleep. Just waits for Dad to finally come home. 

* * *

A boy, a junior- so at least a year older than Dean, sits down at his table in study hall. He never uses the class to study- more like catch up on sleep- but no one ever sits with him.

“Hey...” Dean nods, giving him a quick smile. Percy- his name is Percy- he thinks.

“Hi Dean.” His smile is thin, but his voice is velvet soft. “We had... gym together, right? Last semester.”

Dean raises his brow. “Yea, I think so.”

“I thought so, it's that face. I couldn’t forget it.”

Dean’s heart starts to beat very, very fast “Ha- uh- yea.” Is all he coughs up.

Percy just smiles, tilting his head.

“So, Dean? What are you... what are you doing this evening?” He asks.

Something in Dean begins to stir. This boy- he isn’t like the jocks he’s “friends'' with. He’s like a chick, but he’s definitely not a chick. He makes Dean feel... he makes him feel a lot. Something he’s still getting used to. He hasn’t told anyone- not that there's anyone to tell.

Dean sits forward, grinning like an idiot.

“Hanging out with you, I guess.”

Percy beams back at him. “Smooth.” He flirts. Percy puts his hand out in front of him, like he wanted Dean to take it. “I’ll pick you up, tonight at 8?”

Dean watches him pull his hand through his hair, thick and braided, with the ends just grazing his shoulders, and a sideways smile.

“Fuck yes.” Dean gasps, not meaning to.

“Where do you live?”

“Oh- uh-“ Dean scrambles for someplace else. “I’ll meet you at Johnson’s Antiques, hows that sound?”

Percy glances down at his hand, and then back at him. “I promise I’m discreet, Dean. If that's what you’re worried about.”

“No I just-“ he hates lying, as much as he does it. “My old man. Old fashioned type. And I got a kid brother.”

Percy nods, understanding. He reaches forward for Dean’s notebook, and scribbles something down. “That's my number.” He winks, before getting up. “I’ll see you at 8.”

Dean’s mouth is dry, and his heart feels like it’s going to shoot straight out his chest. “I’ll see ya then.”

He rips the page out and stuff it in his back pocket.

Dean does not make it to meet Percy. He doesn’t even make it 'til 7 before all hell breaks loose.

Dean takes off with Sam right after school. Sometime during the day Dad left coordinates, and Dean knows they are not close.

It hurts. It really fucking sucks.

Sam sits in the back of the Impala, doing homework he’s never going to get to turn in. Dean thinks it makes him feel better, though.

“Dean do you know how to divide fractions?” Sam asks. He rolls his eyes.

“No, Sammy. Sorry.”

“S’okay.” Sam sighs, scribbling something out on his page. Dean watches him from the rear-view. “We’re not going back- are we?”

Dean sighs, rubbing his hand down his face. He’s worried about Dad. Worried he won’t  _ be _ where he says he is. And he’s feeling really shitty for standing up Percy.

“No. I don’t think so Sam. I think Dad messed up a job there.”

Sam groans, shutting his folder on his work.

“But you keep working on that. Keep those good grades.”

“Why?” Sam gets real annoying with his questions lately. He’s not sure who he gets it from.

“Cause- I dunno Sammy.” Dean groans, feeling like an asshole. “Maybe you’ll wanna go to college one day. Do something with that brain.”

“Dad said-“

“Fuck what Dad says. If you wanna go to school we’ll work it out.” Dean turns around, facing him with the red light glaring on Sam’s face. “You’ll be older, and helluva lot smarter than me.”

Sam smiles, faintly. “If you say so, Dean.”

He turns back. “Bet your ass, Sammy.”

Sam goes to bed past 3. Dean checks them into a hotel, and spends hours making sure everything’s safe. He spends another hour trying to call Dad, with absolutely no luck.

“Well. Dad. Call me back if you’re okay.”

Dean slams the receiver back down. He’s down to his last quarter for the pay phone inside the motel lobby.

Then, he remembers Percy.

He knows it's late, almost morning. But he just... dials it anyways.

“Hullo?” Percy’s sleepy, sweet velvet voice comes through after the 6th ring.

“Hi- Percy. Sorry. I know its late.”

“Dean? Where- what?” He doesn’t sound mad. Confused more than anything.

“I’m sorry. I had to leave town. Family emergency.” Dean rubs the back of his neck, exhausted.

“Oh? Is everything alright?”

God damn it, he’s so fucking nice too.

“Yeah, yeah. My- my grandma’s sick. Cancer. We had to come up.”

“Oh.” Percy’s voice breaks. “Will you- when will you be back?”

“I-“ Dean’s heart hurts. He hates this. “I don’t think I will. I’m real sorry, Percy.”

Percy breathes tightly on the other end, and sighs. “Well, I-“ he chuckles. “Honest, Dean, I was real torn up when you didn’t show. I like you a lot.”

“I like you too, Percy.” He smiles, sinking down against the wall. No one is awake to hear him. “I'm sorry.”

“Don’t apologize. Nothing you could do.”

Dean puts his head in his hands.

“Is your brother okay, in all that? He’s little isn’t he?”

Dean feels his heart break. Percy is way too nice of a guy for him. “He’s okay. Tired. We got here late.”

Percy yawns on the other end.

“Speaking of late- You should go back to bed. I’m sorry for bothering you.”

“Yeah. But, you’re not a bother Dean. I’m gonna miss that pretty face.”

This time, the flirtation makes Dean’s heart ache. His stomach turns. He hates himself.

“I’ll call if I’m ever in town.”

“Oh you better. You owe me a date.” Percy says, before letting a quick silence fall.

Dean hangs up.

It takes him a long time to get up off the floor. But he picks himself up off the floor, and crawls into bed across from Sam.

“You okay, Dean?” Sam whisperers, through the dark.

Dean catches a sob back, breathing deep. “I’m okay. Didn’t hear from Dad though.”

“He’ll be okay.” Sam says, sleepily.

Dean turns away, and feels even more horrible. He can’t deal with crushes- boys- not now. Not when he’s got Sammy to take care of.

Better he doesn’t deal with that at all. No guys. No chicks, not for more than a night. He can deal with it when he’s dead.

* * *

The room is white and bright, when Dean comes too. The first thing he sees is the brightness. And the second Sam. 

“Dean!” Sam jumps forward, going for his hand. The hospital's AC must be turned all the way up, cause he’s freezing now. Its summer, for fucks sake. “How are you feeling?” Sam asks. 

Dean rubs his eyes, foggy and tired. “Okay I guess. What the hell happened?” 

Sam makes a face, glancing down at Dean’s legs. “You’re not gonna be happy.” 

Dean groans, throwing off his blanket, and seeing his right leg, in a full knee to foot cast. “ _ Fucking christ. _ ” 

Dad pulls back the curtain, and he’s got a doctor right behind him. 

Sam straightens up beside Dean, breathing in quick. 

“That was one hell’uva break, kid.” The doctor says, looking between Dean and Dad. “Three separate places. But you’re young, you’ll be as good as new with some physical therapy.” 

“How long do I need this boot?” Dean sighs, rubbing his face. Sam holds his breath. 

“Six to eight weeks, depending on how you heal.” 

Dad groans, barely able to look at Dean. 

He- he barely remembers how he even did it. One minute he had a Spirit across from him, and a cute girl on his arm, next thing he knew he was on the ground, leg bent halfway around and passing out. 

“Thanks, doc. I’ll take him from here.” Is all Dad says. The doctor raises his brows at him. 

“He’s gonna need a-”

“He’ll be fine, doc.” Dad’s voice is scary, and strong. The doctor leaves, shaking his head on the way out. “The hell did you think you were thinking?” Dad turns around on his heel, gritting his teeth. 

“Dad-” Sam gets up. He is fourteen and looks the part: all lanky and awkward and acne ridden. And starting to get mouthy. 

“Sam,” Dean puts his hand out. Then looks at Dad. “I don't know Dad, I-” Dean puts his head in his hands. “You get the son of a bitch?” 

Sam nods, looking away from Dad. 

“Yes. Not that you helped.” Dad pushes a hand in his hair, and then goes to grab his bag. “You two are going to Bobby’s. I can’t have you-”

“DAD!” Sam gets up, pushing his chair half over on the way up. “No way!” 

“Sammy.” Dean sighs. He’d rather not have them fight about this. “Dad’s right, I’m no use with-”

“Dean, c’mon!” Sam yells, throwing his hands around. 

“Sam shut up.” Dean puts his hand out, but Sam just swats it away. 

“Sam you shut your fucking mouth.” Dad takes a step closer to them, and even though Sam’s shoulders are tense like he’s about to throw a punch, he backs off. “Bobby’ll be here to pick you up in a few hours. I gotta hit the road.”

Dean’s heart lurches. “You’re leaving? Where?”

“Idaho. Got word of a string of possessions.” Dad looks him in the eyes. It gives him that horrible feeling that, if they weren’t here, his Dad would be beating him into tomorrow. 

“Okay. When will you be back?” Dean mumbles. 

Dad just turns and groans. “I’ll see you when your leg has healed, alright?” 

And that's the last thing their Dad says to them for a good month and a half. 

Bobby picks the boys up from the hospital, Dean taking up the whole back seat to keep his leg elevated.

“How he get busted up so bad?” Bobby asks Sam, while they must think he’s asleep.

“I… I tripped him up. I was stupid and came running in. He saved my ass.” Sam says, staring down at his hands.

Bobby pats him on the back. “Hey, that's his job kiddo. Don't beat yourself up.” 

Dean feels like his insides are behind drained: halfway to sick and halfway to sleeping for the next six weeks.

“He’s your big brother Sammy.” Bobby smiles. Sam looks up carefully. “Whether you like it or not, if he’s anything like I know him to be: you’re gonna be owing your brother big time for the rest of your lives.”

Sam chuckles. “Yeah. I can take care of myself, though.”

Bobby sighs. “Sure you can, boy.” 

Dean tries not to smile, and give himself away. 

“But you’re brother’s gotta watch out for you. Always has and always will, how I see it.”

“I just wish Dad wasn’t so-“

“Such a hard ass?” Bobby laughs. 

“So controlling.” Sam says, all serious. “Dean can take care of himself. And so can I. We’re not kids anymore.”

Bobby gives Sam a look. “Boy you are just as much of a kid as you were when I first met ya, from where I’m sitting.”

Sam pouts at that. But at least he doesn’t talk back. 

“Your Dad’s doing what's best. And so is Dean. Just in their own way.” 

“I just- I hate being treated like I’m a baby, or something.” 

“Sammy,” Bobby rolls his eyes, grinning. “You are the baby. You’re your Daddy’s baby and Dean’s baby brother. Give them time. You’ll prove yourself.”

Sam just crosses his arms at that, and Dean settles himself in for a long nap. 


	2. and Life is a Fucking Nightmare

**Summary for the Chapter:**

> Dean after high school to Cassie 
> 
> WARNING: this chapter references sex work (based off something Jensen said at a panel about Dean's young adulthood) and an implied suicide attempt. Please don't read if thats going to cause you any harm. <3

Dean goes to close the door, before she grabs the back of his neck.

“Thanks, sweetheart.”

Dean recoils, pulling away. “Yep.”

She pulls out a wad of bills from her pocket, folding them out and sliding her fingers over them before handing them to Dean.

“Thanks.” He says, stuffing the money away as quick as he can.

The woman leans in again, and Dean almost punches her then and there. “No. No I don’t-“

She takes two steps back, seemingly squaring Dean up. Her shoulders tense, then un-tense. It seems like she gives up.

“See you again?” She quirks an eyebrow up. Her voice is ruff (and so is she, Dean thinks. Most women don’t treat him like that.)

Dean shakes his head, grabbing the door handle. “No. Leaving town.” He doesn’t say anything else.

She nods, and turns back. Dean slams the door behind him.

Find dinner. Change clothes. Be back before Dad.

He settles on take-out Chinese. Sammy likes it more than him, but it's just under what he’s made so he can get them a treat too.

_ Pie. _

“Hello sweetie, what can I get for you?” The older woman asks. She’s got a pen and paper, scribbling something down for herself.

“You got apple pie?” He asks, looking into the glass case. He smiles, the same one he uses to turn tricks.

She rolls her eyes. “Course I do, kiddo. For here or to-go?”

“To-go. Thank you m’am.”

“It’ll just be a sec.” She smirks, going to the back room.

Dean leans against the counter, fidgety. That wasn’t a great job. She was not a great woman. And Dad’s been out way longer than he said he would.

She comes back, ‘thank you’ bag in tow, setting it on the counter. Dean sets whats left of his cash on the counter.

"You alright, kid? Heading home?" She asks, her voice soft and tired.

"Mhm... Heading home." Dean sighs. "Gotta bring dinner home."

"Well, you mind yourself okay. Keep outta trouble."

"You mind if I use your bathroom, actually?" Dean smiles, sick and sweet. She points him around the corner.

His back is all clawed up. No more women with claws for a while. He'll have to take care not to change in front of Dad. He's lucky this place is a one stall.

"Hey, Sammy!" Dean calls out, his set of keys jangling against the door. "I got food!"

"Dean!" Sam practically bounces out from around the corner. He looks tired, must have been doing math homework or something. "Where have you been?"

"Out." Dean throws the take-out on the table, but sets the pie down carefully. 

Sam grabs the bag, obviously hungry. Dean’s heart pangs at the thought. He takes the carton for himself. 

“How was school, dude?” Dean asks, settling into the chair across from him. Sam has already dug in. 

“Eh,” He shrugs, wiping his face. “Had a test in geometry but I think I did okay.” 

Dean raises his brow, opening his half of the food. “Just okay?”

“Well, like... “ Sam’s cheeks get red, and he rubs the back of his neck. 

“Don’t be embarrassed, one of us has got to be the cool brother.” 

Just as Dean is about to get punched in the arm by Sam, the door starts rattling. 

They look between each other, and Dean grabs for his gun. Sam gets behind his chair. 

The door cracks open, and it's just Dad. Bloodied and bruised- but alive. 

“Dad-” Dean puts his gun down, and goes to grab Dad under his arm. “Nice to see ya.”

Dad just groans, grabbing his side where his shirt is covered in blood. 

“Hey, hey.” Dean sets him down on the couch, turning to Sam. “Get the first aid kit.”

Sam fumbles with his pockets, looking for his car keys. 

“Now!” 

Sam’s out the front door. 

Dad’s eyes are closed, but he’s breathing, and nowhere else looks too bad. Just a black eye and bloody nose. 

“What the hell happened, man?” Dean runs around the motel, grabbing a towel and running it under the sink in the bathroom. 

“Stabbed.” Dad breathes. 

“Yeah, well duh.” Dean sighs, getting down to clean him up. “What were you after.” 

“Vengeful spirit.” Dad breathes, holding the towel against his open wound. 

Sam comes running in, right on time, as Dean cuts off his Dad’s shirt. The wound isn’t that big, but its deep. Gonna hurt like hell for a couple weeks though. “I’m fine, Dean.” He coughs, and grabs the rubbing alcohol and pours some onto the towel. Dean digs through the box for the last of their surgical tape. 

“Sammy get the vodka outta the cooler.” Dean says, quiet. He’s ripping up tape while Dad prepares the bandage. Sam runs to get that. 

Dean takes another look at the wound. His heartbeats hard against his chest. “Dad I think you’ll need stitches.” 

“To hell with that. Just give me-” Dad snatches the bottle from Sam, taking a big swig. 

Dean just nods, stretching the surgical tape so it's applying as much pressure as it can. 

Dean gets Dad cleaned up, and tells Sam to finish his dinner. Dean makes sure he’s comfortable, gives him a beer from the mini fridge and hopes it won't be infected in the morning. He gives Dad his share of dinner. 

“Dean,” Sam whispers, cornering him in the short hallway to the bathroom. His eyes are a little wild. “Did you even eat?” 

Dean clasps him on the shoulder. “I’m good, man.” 

Sam pouts, but then he looks back at Dad. 

“Go to bed Sammy.” Dean ruffles his hair, which he knows annoys him.

By the time both Dad and Sam are asleep, Dean is starving.    
He gets up, as quiet as he can, and goes to sit outside. He takes the pie and a couple beers out with him though. 

Outside it’s quiet, cool. The motel is stuffy and currently smells like blood. 

Dean puts his head in his hands, and gives into the night. 

* * *

Sam leaves. After a big fight, practically blowing up the apartment they were living out of while he was applying to schools. Dad takes off too, but Dean knows he’ll be back. He’ll be back and it’ll just be the two of them. 

After everything he’s done to keep Sam safe, keep him out of trouble and keep him in school: he never actually thought he’d have to watch him go. He thought- he thought there’d be a way to keep Sam safe and let him go to school. 

He didn’t even say goodbye to Dean. 

“If you walk out that door!” Dad screamed. Dean is between the two of the, grabbing Sam by the back of his collar. Sam tears away, and stands by the door.

“What? What!” Sam shouts, throwing his hands around. All he’s got is a backpack of clothes and a hundred bucks. “What’ll you do?!”

“If you walk out that door: you are not coming back! You hear- SAM.”

Sam grabs the door handle, and Dean only hears it slam on his way out.

No clue when Dad’s going to get back, Dean drains the liquor cabinet. Not that there's anything much to drain, but it’s enough to get him shit faced.

Except- usually when he’s shit faced, he can work himself up to go fuck some girl, or bang some dude that he can’t make eye contact with. But tonight, Dean is feeling everything at once. 

Years, and years of pushing this shit- this fear- down, come bubbling up. A decade of wanting, needing, to feel, blow up right in Dean’s face.

Dean has never, ever been a quitter. Never when shit got hard, never when he wanted nothing more than to escape this. 

But now- now. What’s there to live for? 

Dean feels sick, not sure if it's the alcohol or the crying or what he’s done. Like his stomach is going to burn up. He’s standing in the bathroom, not sure what he’s even doing. 

He looks up, after hanging his head in front of the sink, and gets a long, horrible look at what he’s done. 

His eyes are red, and bloodshot. He’s got horrible bruising down his neck, where-

Dean feels like a failure. In more ways than one. 

He’s not gonna be able to hide that from Dad, he isn’t. He doesn’t know what he can even tell him. 

If he just hadn’t chickkened out. No, no that would’ve been worse- for Dad to find him like that. 

He can say he got in a bar fight, or something. He’ll figure it out. 

For now, he draws a bath. That's the nicest thing about this apartment. 

When he was little, he remembers staying in places with just a shower and a sink. Cleaning baby Sammy up after he ate, or spit up, in a sink or a bucket. 

He’s always thrilled when there's a bath. Easier to keep a baby clean, easier to keep Dean sane. 

_ God he’s gonna miss Sam.  _

What hurts most, is Sam isn’t wrong. Dad is… controlling and treats him like a kid. Doesn’t give either of them a fair shot at anything. Can’t bear to see either of them do anything in their own interest. Dean can’t talk to him about anything, especially after a hunt.    
Celebrating with Dad, though. That's what makes him stay. Having Dad clap him on the shoulder, sneak him a drink under the table, and let Dean sit at the “big boy” table at 10. 

But Sam. Sam has always been too smart for his own good. He could have had it all if their lives weren’t so fucked. And even still, the kid got straight A’s, never got suspended, not even a detention. 

Dean can’t live without Sam. He can’t. 

But Sam is much better off without him. 

* * *

Dean has never been this nervous around a girl in his whole goddamn life. He’s never loved anyone this much. Never felt this close to a person who wasn’t Sam or his Dad. 

He’s going to tell her; convince her he’s not crazy and that if she wants to be with him, all this comes with. 

And he’s got something else, if she does believe him.

He’s convinced himself this is the right thing to do. Dad doesn’t know. He’d kick his ass if he did. But- he loves this girl. He can’t leave her without knowing. 

“Hey baby.” Dean smirks, leaning against her door frame. Cassidy Jane Robinson. He thinks to himself. He’s gotta know her full name for this. 

She’s in a tight fitted tank top, and a flowy skirt, packing up her internship backpack. 

“Hey Dean.” She gives him a sultry smile. “You look nice.”

Dean scoffs, his cheeks getting hot. He’s a little cleaned up, but nothing special. “Yeah well, I can’t take you out in any old thing? Not with a girl like you.”

She groans, her face lighting up at his horrible flirting. “You are so-“

“Handsome? Sexy?”

“Annoying.” She raises her brows, getting up, and kissing him.

Dean holds her, hand pressed on the small of her back.  _ He is fucked.  _

“Well, shall we?” She asks, but she pulls him by his collar down to his car.

They stop by her place, to change clothes. Dean sneaks up with her, after talking to Mr. Robinson and feeling well out of his depth. 

She’s wearing her hair up, and a sexy green dress that isn’t too dolled up for where he can afford to take her. 

“You are beautiful.” He says, watching her do her makeup. “I- I am not good enough for a girl like you.”

She laughs, but Dean feels very serious. “Shut up. I love you.” She leans on her elbow. “And, for what it's worth you are very sexy.” 

Dean grins, and pulls her into his arm.

Dinner goes… well just as well as Dean could have hoped. He’s hopelessly, stubbornly in love with this girl, and she charms him every time she opens her mouth.

He pays, which is a feat, and whisks her away in the impala. 

“So.” Cassie puts her hand on his thigh. “Was there something you wanted to talk about? Or was that a lie?”

Dean chokes. He hates that she can read him like a book. “No, no there was.”

He clears his throat, and she pulls her hand away, looking a little worried.

“I uh- Cassie. I love you, ya know?”

“I know Dean.” She chuckles. 

“Well then, listen to me!” He laughs, swatting her shoulder. She pushes him back in response. “You know, my Dad and me- uh- have a family business.” 

She nods, looking skeptical.

“And-“ he rubs his face.  _ Just get it over with.  _ “I haven’t been entirely honest what we do.”

She raises her brows. “... oh?”

“We, um. Cassie, I know this sounds insane. But I’m only telling you cause I- I love you.”

“Dean what are you-?”

“We hunt monsters. And- and ghosts and other freaky shit.”

He lets that bomb drop, and then feels the fall out erupt in front of him.

Dean starts to feel this falling out of his favour. 

“And- and I know that sounds crazy but, I had to tell you. Cassie. Before I-“

“You what?” She says, voice low and dark. 

“I know it sounds insane, Cassie, I know but you’ve gotta-“

“Dean thats fucking bullshit.” She grabs for her door handle, getting out of the car.

“Cassie it’s not-“ 

“What the hell are you talking about?!” She slams the door, just as he gets out of his.

“Cassie I’m being serious, you have to-“

“Is this a joke? What the fuck Dean?” Cassie steps away from him, when he gets closer. Her eyes are dark, and she crosses her arm across her chest.

“I’m not! I’m not! I promise you-“

“Shut up Dean.” 

She’s- Cassie’s crying. Her face looks- she looks like Dean just broke her heart. He doesn’t even know what he did. 

“I’m not lying, Cassie. I’m not.” 

“This is  _ cruel  _ Dean. You know that? If you want to- to break up with me-“

“I don’t!” He yells.

“If you want to break up with me, you could’ve just let me down like a normal person.” She gasps, between laboured breaths. 

Dean just stands there, mouth wide open, feeling like he just got stabbed or something. 

“Cassie-” 

“SHUT UP.” She shouts, throwing her foot down. “Dean just-” Cassie’s face falls, and she runs her hand down her face. “Just go. That's what you want, right?” 

“Cassie I-” Dean’s heart breaks. He doesn’t know what to say. What to do. The ring in his pocket begins to feel like its burning from the inside. 

“Get- get the fuck out of here Dean. We’re done. You’re fucking crazy.” 

Dean’s eyes widen, and watch as Cassie turns away.

He goes back to their motel. Doesn’t tell Dad, and they leave town the next morning. 


	3. Adulthood, and Other Horrors

**Summary for the Chapter:**

> Dean from Jess's death to falling for Cas. 
> 
> WARNING: this chapter also references/implies sex work and John Winchester usual homophobia

Sam’s asleep in the Impala, after crying his eyes out about Jess. Dean just keeps on driving, like when they were kids. 

It’s great to have him back, it really is. But he never wanted it to be like this. 

Dean had… it’s a stupid pipe dream, he’d never even bother telling. But he wishes Sam could’ve gotten his degree. Settled down with some nice girl; Jess, he guesses. Dean could crash at their place and make sure everything was safe and sound for his couple of nieces or nephews. 

Maybe Dean would have a girl of his own. But, like he said, pipe dream.

He’s just glad to have him back. He really is. 

* * *

They’re working a job. Three different teens, kids, go missing one after another. Disappearances from their jobs: a diner, drug store and a McDonalds.

“Hey, what did you even do. When we were kids?” Sam looks up, pinching his brow at Dean like he does when he’s really asking something only tangentially related.

“What you mean?”

“Like.... you’d go out all the time? Go missing for a couple hours and then turn up right before Dad came back.”

Dean turns away from Sam, gripping his pen. Digging it, unopened, into the table.

“Uh... odd jobs. Y’know.”

Sam can always see right through him. Sometimes he pushes. Well, usually he does.

Every time Dean hopes he won’t.

“C’mon,” Sam eyes him. “You? What’d you spend it on?”

Sometimes Dean wonders if they lived lives even congruent to each other as kids.

“You. Dad.” He shrugs, keeping his eyes off Sammy. “Y’know Dad would leave, be gone forever. You needed to eat.”

Sam cocks his head to the side. “What?”

“I did what I had to do. That’s all.” Dean sighs, doing his best to say as little as he possibly can.

“I guess I just... thought Dad left money for you.”

“Ha. Yeah. Never enough.”

Sam frowns. Its the face he makes whenever he’s piecing something together.

It's not a demon. Or a spirit. Or vampires- or fucking anything Supernatural.

It's always horrible when that happens: reminder of how horrible humans can be.

Trafficking. Sam pieces it together not long after they find the kids.

One of the kids, a girl, whose extra shaken up, clings to Dean the entire way out. Barely flinches when he shoots their kidnapper in the back of the head.

She was the one taken first, he realizes, she’d been gone for over two months at that point.

Finally, when they get away from the cops and get this girl to a hospital, she asks Sam and Dean to ride with her.

“Kid- are you-“ Dean stumbles, glancing between her and sam.

“Please.”

She reminds him of Jo, and Cassie, and so they stay crammed up in an ambulance, wait for her to get checked out.

Theres no parents to call, no one to take her home. She's homeless and scared, and Dean's heart breaks for kids like this.

"Hey, kiddo." Dean whispers. She's got her legs curled up tight against her. "Its gonna be okay."

She shakes her head. "I didn't think it was going to go bad... I was just... I needed the money."

Her eyes, wide and so scared, are locked with Dean. He really hopes he doesn't remind her of her Dad or something: he can't be that old.

"Kid I-" Dean fumbles for words. Sam looks like he's lost for words. "I don't know about all this. But I kinda know what thats like. To need money that bad. You did what you had to do."

Her eyes water, and Dean puts his hand on her shoulder. Slow, though, not to scare her.

He's feeling Sam's eyes bore into the back of his head. He's going to hate this conversation on the way home.

"You are gonna be okay though. Look at me, I turned out great." He chuckles, and she gives him a faint smile.

"I didn't think..."

"You are gonna be okay, kiddo. I promise nothing you did was bad. Nothing. You did what was gonna keep you alive and that... that's all we can do."

"So uh... are we gonna talk about that?"

Dean hates Sam sometimes. "Bout what?"

"About... were you lying to her?" His voice breaks, and Dean can tell he's not going to accept anything other than mostly the truth.

Sam's always been smart, always curious. Generally too emotionally intelligent (in his own words) for Dean.

"Sammy I don't wanna-" He hangs his head, groaning at this stupid conversation. Past is the past. "I'm not telling you everything. But I did some things I'm not too proud of to make sure neither of us starved. Or that Dad didn't have anything else on his plate. Okay? Happy?"

He doesn't feel good saying that, can't even bear to look Sam in the eye about it.

Sam is quiet for a while, thank god.

"You are a great older brother. You know that? Always have been." Sam whispers, in his soft, sad voice Dean hates.

He'd give anything for Sam. Anything. That kid better fucking know it.

"Yeah, well-"

"I mean it, Dean." Sam says, strongly. Dean finally glances at him.

"Yeah well. Stop being all sentimental about it, 'kay?"

Sam chuckles, leaning back in his car seat.

Sam falls asleep, like he used to do when they were kids, long before Dean. 

_____________

The moment was coming for a long time. Something he should’ve expected.

Not that that stopped it from hitting him like a ton of bricks.

They’re on a stupid, easy hunt. And Castiel says something so strange. So  _ him _ . And smiles, big and bright with his beautiful eyes. And that's when Dean knows. 

God does he know.

He knows too damn well Cas can’t ever feel the same- so why bother. 

But that doesn’t make it hurt any less. 

Dean loves him. 

He tosses in his sleep thinking about Castiel with him. Can’t keep his eyes from drifting down to his lips. Can’t stop himself from savouring every moment he has alone with Castiel. He’s sure Sam has picked up on at least some of it, with his new sensitivity to making jokes at Dean’s sexuality’s expense. 

He thinks about Cas as soon as he wakes up, eating, drinking, hunting, and always  _ always  _ at night. 

Dean’s hand draws down to his crotch; hard and needy and alone in the bunker. He knows he can’t think too hard about Cas: he’s still not confident the guy can’t read his mind. 

But God- is he thinking. 

Castiel’s hands on his thighs, pressing his thumbs into the divets of Dean’s hips. 

Dean with his hand in Cas’s pretty black hair, messing it up. Cas’s tie undone and his shirt falling open. 

Someone knocks at his door.

Dean, cheeks already red and hot, shouts a half hearted: “Changing!” As he works himself up to look a little presentable. Definitely not like he just came thinking about friend. 

“Hello Dean.” Cas has his brows furrowed, in that way that makes him look very naive: like a puppy. Dean loves it.

“Whats up Cas?” He chokes out. 

“Are you okay?”

Dean coughs, leaning against the door frame. “Yeah- yeah. Why?” 

Cas’s cheeks grow a little pink, but he looks unbothered. “You seemed…. in distress.” 

Dean wants to shoot himself then and there. 

“Ha, no. Must’ve been a nightmare.”

Cas raises his brow, and blinks. Then, his face softens, and he gets  _ that  _ look about him. Dean isn’t sure, still, if its Cas trying to figure him out, or checking him out.

Dean smirks. “Looking to spend the night, buddy?” Feeling his heart jump at the thought. 

Castiel smiles, big and dumb and everything to Dean. “No, no you should rest.” He glances at his shoes, like he’s mimicking embarrassment. “Well. Good night Dean.”

Dean runs his palm down his face, his heart beating way too fast and his cheeks hot. “Night Cas.” 

It's just… it's not. It is not gonna happen. He’s never gonna get a happy ending with Cas. He’s pretty sure happy endings don’t exist in a Winchester storyline anymore. 

So, he says stupid shit. Does reckless, dangerous crap. Gets pretty close to dying just to feel something for once. 

He’s always felt… felt someway about being a little queer. The way hunters talk about it. The way his Dad talked about it. The way everyone  _ assumes  _ he must be “overcompensating” with his jackets and “stoicism.” 

And- the way Sam talked about it. Even if he didn’t- doesn’t know. Dean doesn’t know what’d he’d do with himself if it made things weird between Sam and him. 

And like every other boy, every other emotion: Dean pushing it down beneath a layer of alcohol, jokes and fucking a random girl on the side. 

He’s just never had to push away something so big, like being in love with a man before. It’s like a rock weighing him down on a sinking ship. 

And not just any man,  _ an angel,  _ who will never love him back. 

It hurts not having him. It hurts even more losing him. 


	4. and Then, There Was Cas.

**Summary for the Chapter:**

> Dean from Castiel's death, to his own. And beyond. 
> 
> WARNING: this chapter references suicide and spoilers for 15x18 through 15x20.

Losing Cas. 

Dean has never called himself suicidal. He’s done some things that seem that way. Had other people call him that. But god, does he feel it. 

He has just never wanted to leave Sam behind. 

“Are you… you okay Dean?” Sam whispers, over a beer.

Dean is sitting across him in an ugly, horrible bar. Barely aware of the day let alone what's going on in his head.

He just thinks about Cas, all the goddamn time. 

“Hm?”

“You seems out of it.” Sam says. His eyes are scared. 

“I’ll be okay Sammy.” Dean forces a smile. 

“Dean. You know… you can talk to me. You don’t have to bottle everything up.”

Sam sets his hands down, in front of Dean like a peace offering. Dean hates doing this to him: hates worrying him and hates worrying about him. 

He can’t even begin to muster up a smile. Just stands up to get another round. 

“I’ll be okay Sam. Promise.” 

* * *

Dean lets go. Holding closely to Sam and feeling himself lose. 

Dean has wanted to die for a long time, and when it's finally here. Finally happening. He’s not quite sure how he’s supposed to feel.

Partly, it feels good. To let go and free himself from this stupid, stupid world. But part of him knows it’s killing Sam, to have to see him go. Especially in such a dumb way. 

But: he lets go, and feels himself leave his brother, and the world, behind. 

* * *

Dean takes one of the most serene car rides of his life, Baby running smooth and the radio playing all his favourites. He’s got no clue where he’s going, but he knows he’ll get a feeling when to stop. 

He takes his foot off the gas, and sees he’s stopped at a beach. Warm sand, cool breeze, and  _ Castiel _ standing near the waves. 

Dean’s heart lurches, and before he’s even aware he’s launched himself out of the Impala, running against the sand. 

Castiel turns, just before Dean makes it to him. 

“Hello Dean.” 

Dean grabs his shoulders, and Castiel grabs his forearm, and they collapse into the sand. 

They hold each other like that for a long time. Cas pressing a kiss to Dean’s cheek, before Dean pulls him into one of the messiest kisses in existence. 

“Don’t ever fucking do that to me, Cas. Never again.” Dean demands, grabbing his coat tight. 

Cas smiles, his eyes teary and filled with that kind of love Dean has never, ever seen anyone but his angel have. “I promise. I promise Dean.” 

Dean holds him tight. Holding on for dear life to Castiel. 

“I- I didn’t think you would be here so soon, Dean.” Cas holds him out a little, like he’s taking him in. “You shouldn’t be here so soon.” 

“Cas-”

“You were supposed-”

“Fuck ‘supposed too!’ Cas I’m so fucking tired of destiny and- and fate and your stupid angel trip.” Dean grabs his collar, maybe a little too forcefully ’cause Cas looks frightened by it. He holds Castiel’s face. “I’m here with you, and I am so fucking  _ happy _ .” 

Cas lets out a shaky breath, and lets Dean kiss him, soft and tender like they're supposed to have had. 

“This is my happiest moment. Actually.” Cas coughs, grinning like an idiot. 

They sit by the ocean- or lake… Dean hasn’t asked and he’s not sure if it matters. Cas holds his hand. And everything feels okay, finally. Like the weight of the world has been lifted off his shoulders. 

Except- for Sam. 

He wishes he were here. Safe, and happy, with them,. 

“He won’t be long.” Cas says, softly. Dean turns to him. “But he’ll live a long life. Like you were supposed to.” 

“Thank you. For all of this.” Dean leans his head into Cas’s shoulder. “Time is… different here isn’t it?” he murmurs. 

“Yes. Designed to make the wait as painless as possible.” Cas plays with his hands, grinning and proud. “I promise it won’t be too long.” 

“Just long enough for us to get settled, huh?” Dean chuckles, and Cas smiles. 

* * *

“So, uh, are we gonna talk about this or...?” Sam asks, smiling. Happy and here with Dean. They’re sitting in the living room of Dean and Cas’s cabin. It’s weird to think that. Sam has his feet up on their coffee table, and Dean is across the room at the kitchen island. 

“I can’t ever get a break with you, can I?” Dean laughs, but settles so he’s leaning forward on his elbows. “Go ahead.” He rolls his eyes. 

“How long have you and Cas-”

“Not long. Since we got here.” 

Sam nods, but for Sam ‘not long’ means about 65 years, and for Dean it means about 3. Their incongruence is something they're still getting used too. 

“And… before then?” 

“Sam- what are you getting at?” Dean smirks. This time, Sam’s curiosity is light hearted, makes Dean smile. This place will do that to just about everything. 

“Are you-?”

“I dunno Sammy. Probably bi but what does it matter. Here, anyways.” 

Sam nods, sympathetically. “No, yeah. I just- why didn’t you ever tell me?” 

Dean breaths stiffly, but it doesn’t hurt to talk about anymore. “There wasn’t anything to tell. I wasn’t hooking up with guys and- and I was damn sure Cas wasn’t hooking up with me.” Dean plays with his ring. “And… y’know. By the time you were grown up enough for that, I wasn’t ready to talk about it.” 

“Yeah.” Sam runs a hand up into his hair, smiling. “I’m glad you're happy man. I really, really am.” 

“Me too, Sammy.”

* * *

“Does it ever end?” Dean asks, one night. Cas is close to asleep, curled up against his shoulder. 

“It will. But not for a long time.” Cas mumbles, kissing Dean’s collar. “When everyone on Earth forgets the Winchesters. This will all fade. Which… maybe it won’t ever happen.” 

“Maybe.” Dean kisses his head. “I’ll savor it while we're here, anyways.” 

“I love you, Dean.”

“I love you too, Cas.” 

**Notes for the Chapter:**

> This is my fix-it for the finale.... I have a lot of thoughts *sighs*   
> Love you, thanks for reading <3


End file.
